I think the Santana would be capable and look classy. But, it would be much more difficult to repair or upgrade (things do eventually wear-out). The "Giordano" would likely win-out in some major ride characteristics (weight, stiffness, shifting). Brakes would likely be a wash.
There is a crossover point where an older bike is too old, and the tech outdated such that it just isn't as good as a similarly priced low-tier new bike. I think this case is close to that crossover.